For 13 years, through the darkest days of R. Kelly’s trial for child pornography and the flood of revelations about what The Chicago Sun-Times always called the singer’s pattern of abusing his position of fame and influence to pursue illegal sexual relationships with underage girls, the Chicago superstar’s staunchest defender was his Oak Park-based manager Derrel McDavid.

Now, according to a report by Michelle Manchir in The Chicago Tribune, McDavid is suing Kelly for being late on payments in the settlement the two struck when McDavid broke with Kelly at the end of 2013. Manchir writes that Kelly failed to make his first monthly payment of $40,000 on Aug. 1.

“McDavid has suffered significant harm as a proximate result of Kelly’s breach of the settlement agreement, and is entitled to recover from Kelly the full amount owed,” the lawsuit says.

The total amount R. Kelly owes his former manager under the settlement agreement is about $1.3 million, according to the lawsuit, and the R&B star already paid $300,000 when the agreement was initially executed, the lawsuit says.

The suit seeks payment from R. Kelly to his former manager of the total amount still owed from the agreement, attorneys’ fees and “further relief as is just and appropriate,” the lawsuit says.

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Eric Macey, an attorney for Winkler & McDavid. Ltd., said Monday that the lawsuit “speaks for itself. Mr. Kelly promised to repay a substantial debt that he owes… and now has failed to keep his promise.”

Here’s Kelly's big problem: We’re told McDavid was deeply involved in Kelly’s professional and personal life, and knows everything about the various disputes he’s had with women and others going back 20 years. Sources connected with the case say Kelly could be playing with fire by stiffing McDavid.